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Collect. Czech. Chem. Commun. 2006, 71, 859-870

Kinetics and Mechanisms for the Isomerization of Internucleosidic 3'-O-P-CH2-5' and 3'-O-P-CH(OH)-5' Linkages to Their 2',5'-Counterparts

Tuomas Lönnberga, Šárka Králíkováb, Ivan Rosenbergb and Harri Lönnberga,*

a Department of Chemistry, University of Turku, 20014 Turku, Finland
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech Republic

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  • Lain Luigi, Lönnberg Harri, Lönnberg Tuomas: Intramolecular Participation of Amino Groups in the Cleavage and Isomerization of Ribonucleoside 3′-Phosphodiesters: The Role in Stabilization of the Phosphorane Intermediate. Chem. Eur. J. 2013, 19, 12424. <>
  • Ames Brian D., Nguyen Chi, Bruegger Joel, Smith Peter, Xu Wei, Ma Suzanne, Wong Emily, Wong Steven, Xie Xinkai, Li Jesse W.-H., Vederas John C., Tang Yi, Tsai Shiou-Chuan: Crystal structure and biochemical studies of the trans-acting polyketide enoyl reductase LovC from lovastatin biosynthesis. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 11144. <>
  • Lönnberg Harri: Cleavage of RNA phosphodiester bonds by small molecular entities: a mechanistic insight. Org Biomol Chem 2011, 9, 1687. <>
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  • Edwards David R., Tsang Wing-Yin, Neverov Alexei A., Brown R. Stan: On the question of stepwise vs. concerted cleavage of RNA models promoted by a synthetic dinuclear Zn(ii) complex in methanol: implementation of a noncleavable phosphonate probe. Org. Biomol. Chem. 2010, 8, 822. <>
  • Feng Guoqiang, Tanifum Eric A., Adams Harry, Hengge Alvan C., Williams Nicholas H.: Mechanism and Transition State Structure of Aryl Methylphosphonate Esters Doubly Coordinated to a Dinuclear Cobalt(III) Center. J. Am. Chem. Soc. 2009, 131, 12771. <>
  • Linjalahti Heidi, Feng Guoqiang, Mareque-Rivas Juan C., Mikkola Satu, Williams Nicholas H.: Cleavage and Isomerization of UpU Promoted by Dinuclear Metal Ion Complexes. J. Am. Chem. Soc. 2008, 130, 4232. <>
  • Ora Mikko, Lönnberg Tuomas, Florea-Wang Diana, Zinnen Shawn, Karpeisky Alexander, Lönnberg Harri: Bisphosphonate Derivatives of Nucleoside Antimetabolites: Hydrolytic Stability and Hydroxyapatite Adsorption of 5′-β,γ-Methylene and 5′-β,γ-(1-Hydroxyethylidene) Triphosphates of 5-Fluorouridine and ara-Cytidine. J. Org. Chem. 2008, 73, 4123. <>